Pyrrolidine → 5-(4-Chloro-phenyl)-2-[3-methyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

HRID 271721Notes

Reaction equation

HRID 271721 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:19][N:18]=2)=[CH:11][C:10]=1[CH3:30])(=O)=O.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[CH:21]=[CH:22][C:17]([C:16]#[C:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[C:10]([CH3:30])[CH:11]=3)=[N:18][CH:19]=2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 865946832-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethyl methanesulfonate

Product 1

HCID 598357455-(4-Chloro-phenyl)-2-[3-methyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

Procedure

A solution of 110 mg (0.25 mmol) 2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl methanesulphonate in 2.11 mL (25 mmol) pyrrolidine is heated to 70° C. for 3 h. The mixture is evaporated down i.vac., the residue is combined with water, extracted exhaustively with DCM and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated and after recrystallisation from EtOH the desired product is obtained.

Workup

  1. customThe mixture is evaporated down i.vac
  2. extractionextracted exhaustively with DCM
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customafter recrystallisation from EtOH the desired product
  5. customis obtained

Sources & evidence

ORD record
ord-0d5a1718a731409d9b14662c7e4d6b6f
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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